JPH01132541A - Novel diepoxide and diphenoxy compound - Google Patents

Novel diepoxide and diphenoxy compound

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Publication number
JPH01132541A
JPH01132541A JP63251031A JP25103188A JPH01132541A JP H01132541 A JPH01132541 A JP H01132541A JP 63251031 A JP63251031 A JP 63251031A JP 25103188 A JP25103188 A JP 25103188A JP H01132541 A JPH01132541 A JP H01132541A
Authority
JP
Japan
Prior art keywords
bis
group
naphthol
carbon atoms
anthrol
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Pending
Application number
JP63251031A
Other languages
Japanese (ja)
Inventor
Kenneth C Dewhirst
ケネス・カール・デウイールスト
Jr Thomas G Stewart
トーマス・グローヴス・スチユワート、ジユニア
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Shell Internationale Research Maatschappij BV
Original Assignee
Shell Internationale Research Maatschappij BV
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Filing date
Publication date
Application filed by Shell Internationale Research Maatschappij BV filed Critical Shell Internationale Research Maatschappij BV
Publication of JPH01132541A publication Critical patent/JPH01132541A/en
Pending legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C35/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring
    • C07C35/22—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring polycyclic, at least one hydroxy group bound to a condensed ring system
    • C07C35/23—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring polycyclic, at least one hydroxy group bound to a condensed ring system with hydroxy on a condensed ring system having two rings
    • C07C35/36—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring polycyclic, at least one hydroxy group bound to a condensed ring system with hydroxy on a condensed ring system having two rings the condensed ring system being a (4.4.0) system, e.g. naphols
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C39/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
    • C07C39/12—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic with no unsaturation outside the aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C39/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
    • C07C39/12—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic with no unsaturation outside the aromatic rings
    • C07C39/14—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic with no unsaturation outside the aromatic rings with at least one hydroxy group on a condensed ring system containing two rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C39/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
    • C07C39/12—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic with no unsaturation outside the aromatic rings
    • C07C39/17—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic with no unsaturation outside the aromatic rings containing other rings in addition to the six-membered aromatic rings, e.g. cyclohexylphenol
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
    • C07D303/02—Compounds containing oxirane rings
    • C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
    • C07D303/18—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by etherified hydroxyl radicals
    • C07D303/20—Ethers with hydroxy compounds containing no oxirane rings
    • C07D303/24—Ethers with hydroxy compounds containing no oxirane rings with polyhydroxy compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
    • C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
    • C08G59/22—Di-epoxy compounds
    • C08G59/24—Di-epoxy compounds carbocyclic
    • C08G59/245—Di-epoxy compounds carbocyclic aromatic
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
    • C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
    • C08G59/22—Di-epoxy compounds
    • C08G59/30—Di-epoxy compounds containing atoms other than carbon, hydrogen, oxygen and nitrogen
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2603/00—Systems containing at least three condensed rings
    • C07C2603/02—Ortho- or ortho- and peri-condensed systems
    • C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
    • C07C2603/22—Ortho- or ortho- and peri-condensed systems containing three rings containing only six-membered rings
    • C07C2603/24—Anthracenes; Hydrogenated anthracenes

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Epoxy Compounds (AREA)
  • Epoxy Resins (AREA)

Abstract

NEW MATERIAL: The bis-9-anthrol or bis-ortho-naphthol expressed by formula I or formula II (X1, X2 are each an alkyl, F, Cl; m is 0 to 2; m is 0 to 4; A is an alkylene, a bivalent group consisting of a nonaromatic carbon cyclic group fused to a nonaroamtic or arm. carbon cyclic ring which includes central 5- to 7-membered rings and is crosslinked at need, etc.), or the keto tautomer of the formula I.
EXAMPLE: α,α'-Bis(9-oxo-1-anthryl)-p-diisopropylbenzene.
USE: A monomer for production of a thermoplastic polymer compsn. having a thermosetting treatment characteristic.
PROCESS: The compd. of the embodiment is obtd. by reacting, for example, anthrone, bis-p-(1-hydroxy-1-methylethyl)benzene(p-diol) and 1,1,2-trichloroethane with each other.
COPYRIGHT: (C)1989,JPO

Description

【発明の詳細な説明】 〔産業上の利用分野〕 本発明は、熱硬化性の処理特性を有する新規な熱可塑性
重合体組成物を製造する際に用いうる新規なジエＩキシ
ドおよびジフェノキシ化合物に関する。特に本発明は、
新規なビス−アンスロール、ビス−ナフトールおよびそ
のグリシジルエーテルに関する。DETAILED DESCRIPTION OF THE INVENTION [Industrial Application] The present invention relates to novel die I oxide and diphenoxy compounds which can be used in preparing novel thermoplastic polymer compositions having thermosetting processing properties. . In particular, the present invention
This invention relates to novel bis-anthrol, bis-naphthol and glycidyl ethers thereof.

〔従来の技術〕[Conventional technology]

本出顕人による特願昭６２−１３１９１９号および４２
−／、）／９．！θ号明細書には、新規なジエポキシド
およびジフェノキシ化合物につき熱硬化樹脂組成物が次
の特性を有する必要があると述べられている： ９０℃よシ高い温度における良好な機械的性質；良好な
熱酸化安定性： 良好な耐衝撃性を含む良好な靭性： 良好な疲労特性； 良好な薬品および溶剤耐性； 良好な耐炎性；および 高い耐湿性（たとえば複合体の「高温−湿潤」特性は高
く維持されねばならない）。Patent Application No. 131919 and 42 by Honde Akito
-/, )/9. ! No. θ states that for new diepoxide and diphenoxy compounds, thermosetting resin compositions must have the following properties: good mechanical properties at temperatures above 90°C; good thermal properties. Oxidation stability: Good toughness, including good impact resistance: Good fatigue properties; Good chemical and solvent resistance; Good flame resistance; and high moisture resistance (e.g. the “hot-wet” properties of the composite remain high) must be done).

これらの出願は、単にゲーヒドロキシフェニル誘導体の
使用を開示した実施例を含んでいるに過キス、成る種の
９−ヒドロキシアンスリル〔ビス（デーヒドロキシ−／
θ−アンスリル）−ｐ−ジメチルベンゼン〕並びにパラ
−およびメタ−ヒドロキシ−７−ナフチル誘導体も挙げ
られている。These applications merely contain examples disclosing the use of hydroxyphenyl derivatives, such as 9-hydroxyanthryl [bis(dehydroxy-/
[theta]-anthryl)-p-dimethylbenzene] and para- and meta-hydroxy-7-naphthyl derivatives are also mentioned.

〔発明が解決しようとする課題〕[Problem to be solved by the invention]

本発明の課題は、重合体を製造するだめの選択性を拡大
するとと九ある。The object of the present invention is to expand the selectivity of polymer production processes.

〔課題を解決するための手段〕[Means to solve the problem]

したがって本発明は、 〔式中、ＸｌおよびＸ２はそれぞれ独立して／−４Ｃ個
の炭素原子を有するアルキル基または弗素もしくは塩素
原子を示し、ｍはθ、／もしくはコであり、ｎは０．／
、２．３もしくはなでありかつＡは二価の炭化水素基で
あって （１）３〜ｇ個の炭素原子を有し／、／−置換されてい
ないアルキレン基、 （ｉｉ）　　中央の３〜７眞環を含み、必要に応じ架橋
されまたは非芳香族もしくは芳香族の炭素環リングと融
合した非芳香族炭素環式基から誘導される二価の基、 （ｉｎ）　　７〜２ｑ個の炭素原子を有するジアルキル
芳香族炭素環式基のアルキル基から誘導され、各アルキ
ル基が３〜ｇ個の炭素原子を有しかつ炭素環式基が必要
に応じ架橋されまたは非芳香族もしくは芳香族炭素環リ
ングと融合した中央の芳香族炭素環リングを含む二価の
基、および （ｉｖ）　　７〜２ｑ個の炭素原子を有するジアルキル
非芳香族炭素環式基のアルキル基から誘導され、各アル
キル基が／−ｇ個の炭素原子を有しかつ炭素環式基が必
要に応じ架橋されまたは非芳香族もしくは芳香族炭素環
リングと融合した中央のＳ〜７員の非芳香族環を含む二
価の基 から選択される〕 のビス−９−アンスロールもＬ＜はビス−オルト−ナフ
トールまたは式Ｉａのケト互変異性体廻向けられる。Therefore, the present invention provides the following formula: [wherein Xl and X2 each independently represent an alkyl group having /-4C carbon atoms or a fluorine or chlorine atom, m is θ,/or co, and n is 0. /
, 2.3 or Na, and A is a divalent hydrocarbon group, (1) having 3 to g carbon atoms /, /- unsubstituted alkylene group, (ii) central 3 A divalent group derived from a non-aromatic carbocyclic group containing ~7 true rings, optionally bridged or fused to a non-aromatic or aromatic carbocyclic ring, (in) 7 to 2q Dialkyl aromatic carbocyclic groups having carbon atoms derived from alkyl groups, each alkyl group having from 3 to g carbon atoms, and the carbocyclic group optionally being bridged or non-aromatic or aromatic. a divalent group comprising a central aromatic carbocyclic ring fused to a carbocyclic ring, and (iv) an alkyl group of a dialkyl non-aromatic carbocyclic group having from 7 to 2q carbon atoms, each alkyl dicyclic groups in which the group has /-g carbon atoms and the carbocyclic group contains a central S to 7-membered non-aromatic ring optionally bridged or fused with a non-aromatic or aromatic carbocyclic ring; Bis-9-anthrol of [ selected from the valent groups ] is also directed towards bis-ortho-naphthol or the keto tautomer of formula Ia.

好ましくは、ＸｌおよびＸ２のそれぞれはメチル基もし
くは塩素原子であり、ｍは０もしくは／でありかつｎは
Ｏもしくはｌである。好適具体例において、ｍおよびｎ
は両者とも０である。本明細書の全体を通じて式Ｉａの
ビス−アンスロールだより、このビス−アンスロールと
平衝状態でケト−互変異性体として存在する関連したビ
ス−アンスロンも包含されることに注目すべきである。Preferably, each of Xl and X2 is a methyl group or a chlorine atom, m is 0 or / and n is O or 1. In preferred embodiments, m and n
are both 0. It should be noted that throughout this specification references to bis-anthrone of Formula Ia also include related bis-anthrones that exist as keto-tautomers in equilibrium with this bis-anthrole. be.

好適具体例において、Ａは１２〜２０個の炭素原子を有
するジアルキル芳香族炭素環式基から誘導され、ここで
各アルキル基は３〜３個の炭素原子を有する。アルキレ
ン基、炭素環式基およびジアルキル炭素環式基はユ、２
−イソプロピリデン、アンスリレン、フルオレニレン、
フェニレン−ジイソプロピリデン、ノルカンファニリデ
ン、アダマンチレン、ナフチレンおよび同等な種類の基
を包含する。好ましくは、Ａはフルオレニレン、ナフチ
レンージイソプロピリデンまたはフエニレンージイソプ
ロピリデンである。In a preferred embodiment, A is derived from a dialkyl aromatic carbocyclic group having 12 to 20 carbon atoms, where each alkyl group has 3 to 3 carbon atoms. Alkylene groups, carbocyclic groups and dialkyl carbocyclic groups are
-isopropylidene, anthrylene, fluorenylene,
Includes phenylene-diisopropylidene, norcamphanylidene, adamantylene, naphthylene and similar types of groups. Preferably A is fluorenylene, naphthylene-diisopropylidene or phenylene-diisopropylidene.

ビス−ローナフトールおよびそのジグリジルエーテルが
好適である。何故なら、これらは使用が容易でありかつ
得られるポリエーテルも取扱いが容易であって、極めて
望ましい機械的性質を有するからである。Bis-lonaphthol and its diglydyl ether are preferred. This is because they are easy to use and the resulting polyethers are easy to handle and have very desirable mechanical properties.

弐ｔａのビス−アンスロールおよび式Ｉｂのビス−ナフ
トールは、適当にねおよび心置換されたまたは未置換の
９−アンスロールもしくはｌ−ナフトールを慣用のビス
もしくはそれ以上の官能価のアルキル化剤でアルキル化
して製造することができる。適するアルキル化剤はオレ
フィン、アルコール、ハロダン化炭化水素、カルブニル
化合物などを包含する。たとえば、アルキル化剤はｐ−
シイ７グロ被ニルベンゼン、ビス−ｐ−（／−ヒドロキ
シ−７−メチルエチル）ベンゼン、ビス−ｐ−（／−ク
ロル−／−メチルエチル）ベンゼンなどである。ビス−
アンスロールも、対応の９−アンスロン（すなわちケト
互変異性体）を特にビス−アルコールアルキル化剤によ
シそのヲーヒドロキシ中間体を介しアルキル化して製造
される。Bis-anthrol and bis-naphthol of formula Ib can be prepared by converting a suitably substituted or unsubstituted 9-anthrol or l-naphthol into a conventional bis- or higher-functionality alkylating agent. It can be produced by alkylation. Suitable alkylating agents include olefins, alcohols, halodanated hydrocarbons, carbunyl compounds, and the like. For example, the alkylating agent is p-
Examples include bis-p-(/-hydroxy-7-methylethyl)benzene, bis-p-(/-chloro-/-methylethyl)benzene, and the like. Bis-
Anthrol is also prepared by alkylating the corresponding 9-anthrone (i.e., the keto tautomer) via its hydroxyl intermediate, particularly with a bis-alcohol alkylating agent.

アルキル化は、芳香族アルコールもしくはカルブニル化
合物のアルキル化につき当業界で知られた慣用の方法に
より行なわ扛る。たとえば、９〜アンスロールもしくは
ｌ−ナフトールを、／、／、／　−トリクロル−エタン
、ｐ−）ルエンスルホン酸もしくは塩酸などおよび必要
に応じ３−メルカプトプロピオン酸の存在下に還流させ
ながら適当なビスー第三級アルコール化合物、たとえば
ビス−ｐ−（／−ヒドロキシ−／−メチルエチル）ベン
ゼンで処理する。／−ナフトールの場合、アルキル化は
予想外に殆んど専らフェノール性ヒドロキシル基に対し
オルトの位置で生ずる。Alkylation is carried out by conventional methods known in the art for alkylation of aromatic alcohols or carbunyl compounds. For example, 9-anthrol or l-naphthol is dissolved in a suitable bisulfuric acid solution at reflux in the presence of /, /, / -trichloro-ethane, p-)luenesulfonic acid or hydrochloric acid, etc. and optionally 3-mercaptopropionic acid. Treatment with a tertiary alcohol compound such as bis-p-(/-hydroxy-/-methylethyl)benzene. In the case of /-naphthol, the alkylation unexpectedly occurs almost exclusively at the position ortho to the phenolic hydroxyl group.

さらに本発明は、式［ａおよび式■ｂ：〔式中、Ａ＊　
Ｘ’　＃　Ｘ２＊、ｎおよびｍは上記式１ｍおよびＩｂ
で示したと同じ意味を有する〕によりそれぞれ示される
ビスーアンスロールノシグリシジルエーテルまたはその
ケト互換異性体、およびビス−ナフトールのジグリシジ
ルエーテルにも向けられる。Furthermore, the present invention provides formula [a and formula (ii) b: [wherein A*
X'# X2*, n and m are the above formulas 1m and Ib
It is also directed to bis-anthrol nosiglycidyl ether or its keto tautomer, and to the diglycidyl ether of bis-naphthol, each of which has the same meaning as given above.

上記ジグリシジルエーテルは、対応のビス−アンスロー
ルもしくはビス−ナフトールたとえば水酸化ナトリウム
などフェノールのグリシジル化につき当業界で周知され
た強塩基の存在下でエピクロルヒドリンもしくはエビブ
ロモヒドリンにより処理して製造することができる。反
応は一般に比較的緩和な温度および圧力の条件下で行な
われる。The diglycidyl ethers are prepared by treatment with epichlorohydrin or ebibromohydrin in the presence of strong bases well known in the art for glycidylation of phenols, such as the corresponding bis-anthrol or bis-naphthol, e.g. sodium hydroxide. be able to. The reaction is generally carried out under relatively mild conditions of temperature and pressure.

たとえば、反応は２０〜八ｕ℃にて常圧で行なうことが
できる。ビス−アンスロールモジくはビス−ナフトール
の溶解度に応じて、反応は慣用のアルコール、エーテル
、エステルまたは芳香族もしくは脂肪族炭化水素溶剤な
どの存在下または不□存在下で行なわれる。たとえば、
反応は！ｒθ〜９０℃にてたとえばジエチルエーテル、
トルエン、キシレン、酢酸エチル、イソ酪酸エチル、エ
タノール、特にイソグロノ９ノールのような溶剤中で行
なわれる。For example, the reaction can be carried out at 20-8uC and normal pressure. Depending on the solubility of the bis-anthrolmodylic or bis-naphthol, the reaction is carried out in the presence or absence of customary alcohols, ethers, esters or aromatic or aliphatic hydrocarbon solvents and the like. for example,
What is the reaction? For example, diethyl ether at rθ~90°C
It is carried out in solvents such as toluene, xylene, ethyl acetate, ethyl isobutyrate, ethanol, especially isoglono-9ol.

ビス−アンスロールモジまたとえばエピハロヒドリンを
添加する前にカリウムｔ−ブトキシドを用いて僅か過剰
のビス−アンスロール中にビス−７エネートを生ぜしめ
ることによシ、反応をビス−フェノール互変異性体に好
適となるよう制御しなければ、ケト互変異性体が主たる
生成物となる傾向を有する。Bis-anthrol modifiers can be modified to convert the reaction into bis-phenol tautomers, for example, by using potassium t-butoxide to form the bis-7 enenate in a slight excess of bis-anthrol before adding the epihalohydrin. The keto tautomer will tend to be the predominant product unless controlled to suit.

ビス−ナフトールおよびそのジグリシジルエーテルは、
溶剤抽出などの慣用技術によって精製されかつ回収され
る。ビス−アンスロールおよびそのジグリシジルエーテ
ルは溶剤抽出では精製が若干困難であシ、高純度の物質
が必要とされる場合には慣用のクロマトグラフ技術を用
いる必要がある。Bis-naphthol and its diglycidyl ether are
Purified and recovered by conventional techniques such as solvent extraction. Bis-anthrol and its diglycidyl ether are somewhat difficult to purify by solvent extraction and require the use of conventional chromatographic techniques if high purity material is required.

それぞれ式ＴａもしくはＩｂ、或いはｌｅａもしくはｌ
ｂを有する新規なジエポキシドおよびシフエノキシ化合
物はたとえばポリエーテルアミンおよび／　リエーテル
のような各種の慣用種類の重合体を製造するのに有用で
あシ、さらに上記特許出願疋開示されたような熱硬化性
重合体の特性を有する新規な熱可塑性重合体組成物を製
造するのにも有用である。したがって、これらは主とし
て式： ％式％ 〔式中、Ｙの少なくとも少量（たとえば１０モル％）は
式ＩａもしくはＩｂのビス−アンスロールモジくハヒス
ーナフトールから末端ヒドロキシ基を除去した後に残留
する基であり、Ａ、Ｘ　　、Ｘ　　、ｍおよびｎは上記
の意味を有し、さらにＹの多量（たとえば９０モル％以
下）は異なるビス−フェノール化合物、たと１ｆＪｌる
ビス−アンスロール、ビス−ナフトールもしくは慣用の
ビス−フェノールから末端ヒドロキシ基を除去した後に
残留する基である〕 の反復線状単位で構成された、前記高融点の高分子！ポ
リエーテルまで処理することができる。Formula Ta or Ib, or lea or l, respectively
The novel diepoxide and siphenoxy compounds having b are useful for preparing various conventional types of polymers such as polyether amines and/or lyethers, as well as thermosets such as those disclosed in the above-referenced patent application. It is also useful in making new thermoplastic polymer compositions with polymeric properties. They are therefore primarily of the formula: % [Formula %] where at least a small amount (e.g. 10 mol %) of Y represents the group remaining after removal of the terminal hydroxyl group from the bis-anthrol mojidnaphthol of formula Ia or Ib. , A, X, X, m and n have the meanings given above, and furthermore, a large amount of Y (for example up to 90 mol %) may be a different bis-phenol compound, such as bis-anthrol, bis-naphthol or is the group remaining after removing the terminal hydroxyl group from conventional bis-phenol.] The high melting point polymer is composed of repeating linear units of Can be processed up to polyether.

ポリエーテルもしくはポリエーテルアミン組成物の硬化
性（ｌｆｓ状）分子は、上記特許出願に記載されたよう
に、（１）上記式ＩａもしくはＩｂのビス−アンスロー
ルもしくはビス−ナフトールを異なる慣用のビス−フェ
ノール成分もしくはそのジグリシジルエーテルおよび必
要に応じ多官能性フェノールもしくはアミンと塩基の存
在下で反応させ、或いは（２）ビス−アンスロールモジ
くはビス−ナフトールのジグリシジルエーテルを単独で
、或いは（＆）さらに塩基の存在下で貫用のビス−フェ
ノールと反応させ、或いは（ｂ）ジーｓｅｃアミン成分
単独および必要に応じ多官能性フェノールもしくはアミ
ンと反応させることによシ製造される。必要に応じ、こ
れらの分子は光架＠ＪＣよシ、すなわち１００個の反復
構造につき７〜３０個の架橋種度まで架橋することがで
きる。The curable (lfs-like) molecules of the polyether or polyether amine compositions are prepared by: (1) converting the bis-anthrol or bis-naphthol of formula Ia or Ib above to a different conventional bis-naphthol, as described in the above-mentioned patent application; - reacting with the phenol component or its diglycidyl ether and optionally a polyfunctional phenol or amine in the presence of a base, or (2) the diglycidyl ether of bis-anthrol modi or bis-naphthol alone, or (&) further reacted with a common bis-phenol in the presence of a base; or (b) the G-sec amine component alone and optionally a polyfunctional phenol or amine. If desired, these molecules can be photocrosslinked to a degree of crosslinking of 7 to 30 crosslinks per 100 repeats.

ポリエーテルもしくはポリエーテルアミンの樹脂組成物
は、当業界で知られた方法により溶融物もしくは溶液か
らｕｔ維強化材に施こすことができる。本発明に有用な
各種の方法のうちには、樹脂移動成形（ＲＴＭ　）、引
出成形、フィラメント巻付け、およびプリプレグの使用
が含まｎる。The polyether or polyether amine resin composition can be applied to the UT fiber reinforcement from a melt or solution by methods known in the art. Among the various methods useful in the present invention are resin transfer molding (RTM), pultrusion, filament winding, and the use of prepregs.

〔実施例〕〔Example〕

以下、実施例／−３により本発明の化合物の製造方法に
つき説明する。実施例乙においては本発明による化合物
の好適使用例を示し、この使用は本出願人による前記特
許出願における発明の主題である。Hereinafter, the method for producing the compound of the present invention will be explained using Example/-3. Example B shows a preferred use of the compounds according to the invention, which use is the subject of the invention in the aforementioned patent application by the applicant.

ン（ＢＡＤＢ　） ｆｆｌ　拌ｆｆ応器にアンスロンとビス−ｐ−（／−ヒ
ドロキシ−／−メチルエチル）ベンゼン（ｐ−ジオール
）と７．／、、２−トリクロルエタンとを４：／ニアの
モル比にて充填しかつ窒素および還流凝縮器の下で１０
０℃まで加熱することにより、ＢＡＤＢを合成した。添
加漏斗を用いて７００℃でｆｉ、ｌ１ｌＨＣ６水溶液Ｃ
ｌ００％ＨＣｔとして７０２モル／ｐ−ジオール１モル
）を添加した。濾過（Ｃよ５　ＢＡＤＨを回収し、かつ
メタノールで洗浄し、沸とうトルエン中にスラリーさせ
、濾過しかつメタノールで再び洗浄することによシ精製
した。収率は、融点２３３〜２６５℃を有する黄色微結
晶乙Ｏ％であった。ＢＡＤＢの化学構造は、Ｃ／３固相
ＮＭＲによって確認した。(BADB) ffl Add Anthrone and bis-p-(/-hydroxy-/-methylethyl)benzene (p-diol) to a stirring ff reactor.7. /,,2-trichloroethane in a molar ratio of 4:/nia and under nitrogen and a reflux condenser.
BADB was synthesized by heating to 0°C. fi, l1lHC6 aqueous solution C at 700 °C using an addition funnel.
702 mol/mol of p-diol) was added as 100% HCt. Filtration (C5 BADH was collected and purified by washing with methanol, slurry in boiling toluene, filtering and washing again with methanol. Yield: mp 233-265°C. The chemical structure of BADB was confirmed by C/3 solid-phase NMR.

攪拌反応器に実施例／のＢＡＤＨとカリウムｔ−ブトキ
シ）”　（ＫＴＢＡ　）とトルエンとを／　：　　２．
４１５のモル比で添加しかつ窒素下で７７０℃まで７時
間加熱することによ）、ＤＧＢＡＤＨを合成した。１−
ブタノールをトルエン共沸物として連続除去し、かつ新
たにトルエンを反応器へ添加した。反応物質はこの１穐
においてスラリーを維持したが、色はＢＡＤＡのカリウ
ム塩が生成されるにつれて黄色から深赤色まで変化した
。１１０℃にて１時間後、赤色スラリーをｑ−ｏ′ｃま
で冷却した。添加漏斗によシエビクロルヒドリン（２θ
〜コθＯモル／ＢＡＤＢ　１モル）を１度に全部添加し
、かつこの物質を７０℃にて６０〜９０分間反応させた
。この工種の間、赤色ＢＡＤＢ塩が溶解しかつＫＣｔの
結晶と未変換ＢＡＤＢとが生成した。反応物を最初に冷
却しかつ固体を沈降させることにより、粗生成物を回収
した。上澄液をフィルタにニジデカントし、かつ生成物
を最高１００℃にて／　＝　ｊｍｍＨｇの減圧下で減圧
蒸発させることによシ生底物を回収した（この温度にて
１０分間以内）。この粗生成物２０重重量上メチルイソ
ブチルクトン（ＭＩＢＫ　）に溶解し、かつ洗浄水が中
性となるまで水洗した。ＭＩ　ＢＫを減圧蒸発させて最
終生成物を回収した。得られたＤＧＢＡＤＨはエポキシ
当＃ＣＥＥＷ’）＝３９３〜’ｌ−！；０　　（理論Ｅ
］１Ｗ＝３３／　）と鹸化性塩素（Ｓａｐ　ＣＬ）＝０
．０７重ｉ％と、融点＝ｌ乙Ｏ〜／７０℃とを有した。BADH, potassium t-butoxy) (KTBA) and toluene were added to a stirred reactor: 2.
DGBADH was synthesized by adding at a molar ratio of 415 and heating to 770° C. for 7 hours under nitrogen). 1-
Butanol was continuously removed as a toluene azeotrope and fresh toluene was added to the reactor. The reactants remained a slurry over this period, but the color changed from yellow to deep red as the potassium salt of BADA was formed. After 1 hour at 110°C, the red slurry was cooled to qo'c. In the addition funnel add chlorohydrin (2θ
-1 mole of θO/1 mole of BADB) was added all at once and the material was allowed to react at 70° C. for 60-90 minutes. During this process, the red BADB salt dissolved and crystals of KCt and unconverted BADB were formed. The crude product was recovered by first cooling the reaction and allowing the solids to settle. The raw bottom material was recovered by decanting the supernatant into a filter and evaporating the product under vacuum at a maximum of 100° C./=jmmHg (within 10 minutes at this temperature). This crude product was dissolved in 20% by weight of methyl isobutyl lactone (MIBK) and washed with water until the washing water became neutral. MI BK was evaporated under reduced pressure to recover the final product. The obtained DGBADH is an epoxy compound #CEEW')=393~'l-! ;0 (Theory E
]1W=33/ ) and saponifiable chlorine (Sap CL)=0
．． It had a weight i% of 0.07% and a melting point of lO~/70°C.

ＤＧＢＡＤＢの化学構造は、Ｃ／３溶液ＮＭＲ末端基分
析実験によって証明した。The chemical structure of DGBADB was verified by C/3 solution NMR end group analysis experiments.

攪拌反応器へｌ−ナフトールと９−フルオレノン、！：
　／、／、／　−）　リクロルエタン、！：、ｐ−トル
エンスルホン酸と３−メルカプトプロピオン酸とをｇ：
ｉ：ａ：ｏ、ｓ”、ｏ、ｉのモル比で添加し、かつ窒素
および還流凝縮器の下で９０℃までコ時間加熱すること
により、ＢＮＦＬを合成した。９０℃にて５分間抜に、
結晶が反応物中に生成した。反応物質が結晶を伴なって
固体となった際、さら４Ｃ／、／、／　−トリクロルエ
タンを添加しかつ反応を続行した。l-naphthol and 9-fluorenone into a stirred reactor,! :
/, /, / −) Lichlorethane,! :, g of p-toluenesulfonic acid and 3-mercaptopropionic acid:
BNFL was synthesized by adding in the molar ratio of i:a:o,s”,o,i and heating to 90 °C for a period of time under nitrogen and a reflux condenser. To,
Crystals formed in the reaction. When the reactants became solid with crystals, more 4C/,/,/-trichloroethane was added and the reaction continued.

この反応物をイソグセピルアルコール（１２人）の７部
を添加して冷却し、生成物を濾過により除去しかつ１２
人で洗浄した。　ＢＮＦ’Ｌがｑ１％収宅で融点＝２．
４ｇ−２９０℃の白色結晶として得られた。The reaction was cooled by adding 7 parts of isogosepyl alcohol (12 parts), the product was removed by filtration and 12 parts of
Washed by humans. Melting point of BNF'L at q1% = 2.
4g - 290°C white crystals were obtained.

ＢＮＦＬの化学構造は、Ｃ／３および７”　ｃｌ）ン溶
液ＮＭＲによって証明した。The chemical structure of BNFL was verified by C/3 and 7'' solution NMR.

ン（ＢＮＤＢ　） 攪拌反応器へｌ−ナフトールとビス−ｐ−（／−ヒドロ
キシ−７−メチルエチル）ヘンゼン（Ｐ−ジオール）と
ヘムコーもしくはヘム／−）リクロルエタンとをｇ：／
：＆のモル比で添加しかつ窒素および還流凝ｍ器の下で
り０℃まで加熱することにより、ＢＮＤＢを合成した。(BNDB) l-naphthol, bis-p-(/-hydroxy-7-methylethyl)henzen (P-diol) and hemco or hem/-)lichloroethane in g:/ to a stirred reactor.
BNDB was synthesized by adding in a molar ratio of :& and heating to 0° C. under nitrogen and a reflux condenser.

添加漏斗によシフ０’Ｃ／Ｃて濃厚ＨＣ１水溶液（７０
０％　ＨＣｔとして７０２モル：ｐ−ジオール１モル）
を添加した。Add concentrated HC1 aqueous solution (70
702 mol as 0% HCt: 1 mol of p-diol)
was added.

この反応物質を、ＨＣｌの添加が完了した後に１時間に
わたシＩｒθ℃で加熱した。最初のＨＣＡを添加してか
ら７０〜７３分間後に１反応物質からＢＮＤＢ結晶が分
離し始めた。７時間の後、反応器はＢＮＤＢ結晶で満た
された。スラリーが冷却されるにつれてｒＰＡを添加す
ることによシ、ＢＮＤＢの濾過を促進させた。濾過によ
シＢＮＤＢを回収し、かつｒＰＡで数回洗浄した（白色
となるまで）。Ｆ液を沸とうｒＰＡ中にスラリー化させ
、かつ再び濾過して集めた。融点＝２’ｌ！ｒ　〜２！
ｒ！ｒ℃の白色結晶ＢＮＤＢＣ９０〜９夕鴨収率）は、
エポキシ樹脂を作成するのに適する純度であった。さら
Ｋ　ＢＮＤＢをテトラヒドロフランから再結晶化させた
（　ｉ　１Ｉｉｌ１％ＢＮＤＢ　）。ＢＮＤＢの化学構
造は、Ｃ／３およびプロトン溶液ＮＭＲとＸＩｓ回折と
中赤外実験とにより確認した。The reaction mass was heated at Irθ° C. for 1 hour after the addition of HCl was complete. BNDB crystals began to separate from one reactant 70-73 minutes after the first HCA addition. After 7 hours, the reactor was filled with BNDB crystals. Addition of rPA as the slurry cooled facilitated BNDB filtration. BNDB was collected by filtration and washed several times with rPA (until white). Solution F was slurried in boiling rPA and filtered and collected again. Melting point = 2'l! r~2!
r! The white crystal BNDBC90-9 Yuga yield at r°C is
The purity was suitable for making epoxy resin. Further KBNDB was recrystallized from tetrahydrofuran (i1Iil1%BNDB). The chemical structure of BNDB was confirmed by C/3 and proton solution NMR, XIs diffraction, and mid-infrared experiments.

攪拌反応器へＢＮＤＢとエピクロルヒドリン（部層）と
イソプロノぐノール（１２人）と水とをｌθ二ｉｓ、。Add BNDB, epichlorohydrin (partial), isopronol (12), and water to a stirred reactor.

：／３．ｊ：／ユＯのモル比で添加しかつ窒素および還
流凝縮器の下で７０ｃまで加熱することにより、ＤＧＢ
ＮＤＢを作成した。７０℃にて反応物質はスラリーとな
った。コＯ重量鴨の水酸化ナトリウム（ＢＮＤＢ　１モ
ル当！７　、？、　０モルの水酸化ナトリウム）を熱反
応物質へ５０分間にわたって段階的に添加した。ＢＮＤ
Ｂは、最初のＮａＯＨ添加の終了時点で溶液まで反応し
た。有機相を熱脱イオン水によシ洗浄水が中性となるま
で洗浄した。有機相が冷却されかつより濃縮された際、
　ＤＧＢＮＤＢ結晶は溶液から分電する傾向を有した。:/3. The DGB
Created NDB. At 70°C, the reactants became a slurry. Sodium hydroxide (0 moles of sodium hydroxide per mole of BNDB) was added stepwise to the hot reactants over a period of 50 minutes. BND
B reacted to solution at the end of the first NaOH addition. The organic phase was washed with hot deionized water until the wash water was neutral. When the organic phase is cooled and becomes more concentrated,
DGBNDB crystals had a tendency to dissipate from solution.

ＤＧＢＮＤＢを含有する有機相を減圧蒸発して、Ｅ１ｉ
Ｗ＝、？／ＡとＳａｐ　ＣＬ＝０．０４１〜θθ６重ｆ
ｆｉ％とを有する所望の生成物を得た。この生成物をメ
チル−インブチルケトン（ＭＩＢＫ　）と２０〜３０ｆ
量鳴の樹脂に溶解させ、かつ５重量％のＮａＯＨ水溶液
を用いて第２回の脱ハａｙン化反応を行なった。この樹
脂溶液を窒素下で２０〜２３重量％（樹脂溶液の重量に
対し）の！重量１ＮａＯＨ水溶液と共に２時間にわたり
加熱還流させた。The organic phase containing DGBNDB was evaporated under reduced pressure to obtain E1i
W=,? /A and Sap CL=0.041~θθ6fold f
The desired product with fi% was obtained. This product was mixed with methyl-imbutyl ketone (MIBK) and 20-30f
A second dehydration reaction was carried out using a 5% by weight aqueous NaOH solution. This resin solution was prepared under nitrogen at a concentration of 20-23% by weight (relative to the weight of the resin solution). Heated to reflux for 2 hours with 1 wt. of NaOH aqueous solution.

塩水を除去しかつ樹脂溶液を熱脱イオン水によシ洗浄水
が中性となるまで洗浄した。この熱樹脂溶液を一過して
全ての不溶性物質を除去し、次いで蒸留により約３０重
量鴨の樹脂まで濃縮した。溶液が冷却する際に生成した
ＤＧＢＮＤＢ結晶を濾過によシ集めた。この白色結晶Ｄ
ＧＢＮＤＢはＥＥＷ＝コざ／（理論）Ｐ５ｉ＝コク９）
とＢａｐＣ１＝＜０．０部重量鴨と融点：／１，７〜Ｉ
＆ｇ℃とを有した。ＤＧＢＮＤＢの化学構造は、Ｃ／３
およびプロトン溶液ＮＭＲＫよシ確認した。The brine was removed and the resin solution was washed with hot deionized water until the wash water was neutral. The hot resin solution was passed through to remove all insoluble material and then concentrated by distillation to approximately 30 weight duck resin. DGBNDB crystals formed as the solution cooled and were collected by filtration. This white crystal D
GBNDB is EEW=Koza/(theory) P5i=Koku9)
and BapC1=<0.0 part weight duck and melting point: /1,7~I
&g°C. The chemical structure of DGBNDB is C/3
and proton solution NMRK.

実施例６： 各種のフェノール性硬化剤およびアミン硬化剤を用いて
、本発明によるジグリシジルエーテルを次のように重合
させた： 単量体を１９９℃にて減圧３角フラスコ内に所望の化学
量論量で溶解しかつ硬化剤で処理することによ？）　、
　ＤＧＢＮＤＢ　／アミン重合体を作成し友。溶解が生
じている際、３角フラスコに減圧ポンプを施こしく／〜
５ｍＨｒ：の減圧）かつ脱気することによシ、混合を促
進させた。フェノール性硬化剤によシ作成されたＤＧＢ
ＮＤＢ系重合体の場合には、単量体が溶解されかつ均質
となった後１ｃ　ＭＢＴＰＰ　（メチｔ／７−ヒス−）
＋７フエニルホスフインジブロマイド；０．００．μ当
量のＢｒ　／エポキシｌ当量）を添加した。重合体（特
記しない限シ）は、強制通気オープン内で７９０℃にて
２１時間硬化させた・プレＩリマ混合物をスルファシル
（登録商標）シリコーン処理剤（ピアス・ケミカル・カ
ンパニー社）で予備処理された予熱ガラス板の間に注い
だ。これらガラス板を馬蹄形の３１ｍテフロン（登録商
標）ピース−で分離させてクランプ固定した。Example 6: Diglycidyl ethers according to the invention were polymerized using various phenolic and amine curing agents as follows: The monomers were added to the desired chemistry in a vacuum Erlenmeyer flask at 199°C. By dissolving in stoichiometric amounts and treating with a hardening agent? ),
DGBNDB / A friend who creates amine polymers. When dissolution occurs, apply a vacuum pump to the Erlenmeyer flask.
Mixing was facilitated by vacuum (vacuum of 5 mHr) and degassing. DGB made with phenolic curing agent
In the case of NDB-based polymers, after the monomers are dissolved and homogeneous, 1c MBTPP (methyt/7-his-)
+7 phenylphosphine dibromide; 0.00. μ equivalent of Br/epoxy l equivalent) was added. Polymers (unless otherwise specified) were cured for 21 hours at 790°C in a forced-air open air system.Pre-I lima mixtures were pretreated with Sulfacyl® silicone treatment (Pierce Chemical Company). Pour between preheated glass plates. These glass plates were separated and clamped using a horseshoe-shaped 31 m Teflon (registered trademark) piece.

全範囲の機械的試験に対する典型的な注型寸法は’１−
０１とした。得られた組成物を下表に示す。Typical casting dimensions for the full range of mechanical testing are '1-
It was set to 01. The resulting composition is shown in the table below.

得られたポリエーテル熱可塑性組成物は、溶剤耐性を含
む向上した性質のバランスおよび向上したモジュラス／
がラス遷移温度／靭性のバランスと共に、熱硬化性重合
体の特徴を有した。The resulting polyether thermoplastic compositions exhibit an improved balance of properties including solvent resistance and improved modulus/
It had the characteristics of a thermosetting polymer with a balance of lath transition temperature/toughness.

ＤＧＢＮＤＢ　　α、α′−ビス（／−ヒドロキシ−ニ
ーナフチル）−ｐ−ジイソプロピルベンゼンの　。DGBNDB α,α′-bis(/-hydroxy-ninaphthyl)-p-diisopropylbenzene.

ジグリシジルエーテル ＨＭＡＤＢ　　α、α′−ビス（Ｎ−メチル−クーアミ
ノフェニル）−ｐ−ジイソプロピルベンゼンＡＤＢ　　
　α、α′−ビス（ｔ−アミノフェニル）−ｐ−ジイソ
プロピルベンゼン（エポン硬化剤ＨＰＴ　１０乙／） ＢＰＤＢ　　　α、α′−ビス（クーヒドロキシフェニ
ル）−ジイソプロピルベンゼン ＴＰＴＢ　　　α、α′、α〃−トリス（４−ヒドロキ
シフェニル’）　−／、３．３−トリイソプロピルベン
ゼン ＢＰＡ　　　２，２−ビス（ｑ−ヒドロキシフェニル）
プロパン ＤＭＡ　　　２．Ａ−ジメチルアニリンＤＭＡＤＢ　　
α、α′−ビス（クーアミノ−３，３−ジメチルフエニ
ル）−ｐ−ジイソプロピルベンゼン（エポン硬化剤）　
ＨＰＴ　１０４２　）ＮＢＭＤＡ　　Ｎ、Ｎ’−ジー５
ｅａ−ブチルメチレンジアニリン ＴＨＱ　　　／、２，３．Ｉｔ−テトラヒドロキノキサ
リン。Diglycidyl ether HMADB α,α′-bis(N-methyl-quaminophenyl)-p-diisopropylbenzene ADB
α, α′-bis(t-aminophenyl)-p-diisopropylbenzene (Epon curing agent HPT 10/) BPDB α, α′-bis(t-hydroxyphenyl)-diisopropylbenzene TPTB α, α′, α〃- Tris(4-hydroxyphenyl') -/, 3,3-triisopropylbenzene BPA 2,2-bis(q-hydroxyphenyl)
Propane DMA 2. A-dimethylaniline DMADB
α, α′-bis(kuamino-3,3-dimethylphenyl)-p-diisopropylbenzene (Epon curing agent)
HPT 1042) NBMDA N, N'-G5
ea-butylmethylene dianiline THQ/, 2,3. It-tetrahydroquinoxaline.

Claims (6)

【特許請求の範囲】[Claims] （１）式 I ａもしくは I ｂ： ▲数式、化学式、表等があります▼ I ａ▲数式、化学
式、表等があります▼ I ｂ 〔式中、Ｘ＾１およびＸ＾２はそれぞれ独立して１〜４
個の炭素原子を有するアルキル基または弗素もしくは塩
素原子を示し、ｍは０、１もしくは２であり、ｎは０、
１、２、３もしくは４であり、かつＡは二価の炭化水素
基であつて （ｉ）３〜８個の炭素原子を有し１，１−置換されてい
ないアルキレン基、 （ｉｉ）中央の５〜７員環を含み、必要に応じ架橋され
または非芳香族もしくは芳香族の炭素環リングと融合し
た非芳香族炭素環式基から誘導される二価の基、 （ｉｉｉ）７〜２４個の炭素原子を有するジアルキル芳
香族炭素環式基のアルキル基から誘導され、各アルキル
基が３〜８個の炭素原子を有しかつ炭素環式基が必要に
応じ架橋されまたは非芳香族もしくは芳香族炭素環リン
グと融合した中央の芳香族炭素環リングを含む二価の基
、および （ｉｖ）７〜２４個の炭素原子を有するジアルキル非芳
香族炭素環式基のアルキル基から誘導され、各アルキル
基が１〜８個の炭素原子を有しかつ炭素環式基が必要に
応じ架橋されまたは非芳香族もしくは芳香族炭素環リン
グと融合した中央の５〜７員の非芳香族環を含む二価の
基 から選択される〕 のビス−９−アンスロールもしくはビス−オルト−ナフ
トールまたは式 I ａのケト互変異性体。(1) Formula I a or I b: ▲There are mathematical formulas, chemical formulas, tables, etc.▼ I a▲There are mathematical formulas, chemical formulas, tables, etc.▼ I b [In the formula, X^1 and X^2 are each independently 1-4
represents an alkyl group or a fluorine or chlorine atom having 4 carbon atoms, m is 0, 1 or 2, n is 0,
1, 2, 3 or 4, and A is a divalent hydrocarbon group (i) a 1,1-unsubstituted alkylene group having 3 to 8 carbon atoms; (ii) a central a divalent group derived from a non-aromatic carbocyclic group, optionally bridged or fused with a non-aromatic or aromatic carbocyclic ring, (iii) 7-24 derived from the alkyl group of a dialkyl aromatic carbocyclic group having 3 to 8 carbon atoms, each alkyl group having 3 to 8 carbon atoms and the carbocyclic group optionally being bridged or non-aromatic or derived from a divalent group comprising a central aromatic carbocyclic ring fused to an aromatic carbocyclic ring, and (iv) an alkyl group of a dialkyl non-aromatic carbocyclic group having from 7 to 24 carbon atoms; A central 5- to 7-membered non-aromatic ring in which each alkyl group has 1 to 8 carbon atoms and the carbocyclic group is optionally bridged or fused with a non-aromatic or aromatic carbocyclic ring. bis-9-anthrol or bis-ortho-naphthol or the keto tautomer of formula Ia. （２）Ｘ＾１およびＸ＾２がそれぞれ独立してメチル基
または塩素原子を示す請求項１記載のビス−アンスロー
ルもしくはビス−ナフトール。(2) The bis-anthrole or bis-naphthol according to claim 1, wherein X^1 and X^2 each independently represent a methyl group or a chlorine atom. （３）ｍおよびｎが０である請求項ス記載のビス−アン
スロールもしくはビス−ナフトール。(3) The bis-anthrol or bis-naphthol according to claim 1, wherein m and n are 0. （４）Ａが１２〜２０個の炭素原子を有するジアルキル
芳香族炭素環式基から誘導され、各アルキル基が３〜５
個の炭素原子を有する２価の基であり、さらにアンスロ
ールもしくはナフトールが前記ジアルキル芳香族炭素環
式基のアルキル置換基に結合している請求項３記載のビ
ス−アンスロールもしくはビス−ナフトール。(4) A is derived from a dialkyl aromatic carbocyclic group having 12 to 20 carbon atoms, each alkyl group having 3 to 5
4. The bis-anthrole or bis-naphthol of claim 3, wherein the bis-anthrol or bis-naphthol is a divalent radical having 100 carbon atoms, and the anthrol or naphthol is further bonded to the alkyl substituent of the dialkyl aromatic carbocyclic group. （５）Ａがフェニレン−ｐ−ジイソプロピリデン基であ
る請求項５記載のビス−ナフトール。(5) The bis-naphthol according to claim 5, wherein A is a phenylene-p-diisopropylidene group. （６）請求項１〜５のいずれか一項に記載のビス−アン
スロールもしくはビス−ナフトールの式IIａもしくはI
Iｂ： ▲数式、化学式、表等があります▼IIａ ▲数式、化学式、表等があります▼IIｂ を有するジグリシジルエーテル。(6) Formula IIa or I of bis-anthrol or bis-naphthol according to any one of claims 1 to 5.
Ib: ▲There are mathematical formulas, chemical formulas, tables, etc.▼IIa ▲There are mathematical formulas, chemical formulas, tables, etc.▼IIb Diglycidyl ether with.
JP63251031A 1987-10-09 1988-10-06 Novel diepoxide and diphenoxy compound Pending JPH01132541A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US107,618 1987-10-09
US07/107,618 US4847011A (en) 1987-10-09 1987-10-09 Bis-anthrols and bis-naphthols and diglycidyl ethers thereof

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JPH01132541A true JPH01132541A (en) 1989-05-25

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US (1) US4847011A (en)
EP (1) EP0311212A3 (en)
JP (1) JPH01132541A (en)
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CA (1) CA1304077C (en)

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Also Published As

Publication number Publication date
EP0311212A2 (en) 1989-04-12
US4847011A (en) 1989-07-11
KR890006552A (en) 1989-06-13
EP0311212A3 (en) 1990-10-03
CA1304077C (en) 1992-06-23

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